The purpose of this study was to examine the relationship between high school and collegiate organizational involvement and their effects on leader self-efficacy, motivation to lead and leadership skill. The study investigated student members of registered student organizations during Fall 2016. Results of the study indicated strong relationships between past high school involvement, current collegiate involvement and leadership development. Positional leadership and priority of engagement during high school were predictive of leader skill and self-efficacy. The study also found that mental and physical engagement in college organizations predicted leader motivations and skills. This study was conducted to understand how the leadership development process is effected at different points in time over young adulthood and should continue to be studied for greater insights into how to unlock the leadership potential in young adults more intentionally.